Logan International Airport
Boston, United States
O'Hare International Airport
Chicago, United States
$131 USD
-55%$59 USD
Verified Nov 30, 2025 at 7:34 AMRare Availability
7% of dates checked are available within 10% of the lowest price
Tuesday, January 20th, 2026
Outbound Flights
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3h 11m·Nonstop
$203 USD
BOSJan 20 12:55
→ORDJan 20 15:06
AA 4074Embraer 175
3h 15m·Nonstop
$203 USD
BOSJan 20 15:50
→ORDJan 20 18:05
AA 4157Embraer 175
5h 1m·1 stop
$213 USD
BOSJan 20 10:00
→DCAJan 20 11:59
AA 3790Embraer 175
45m layover

DCAJan 20 12:44
→ORDJan 20 14:01
AA 1944Airbus A319
4h 52m·1 stop
$213 USD
BOSJan 20 07:00
→DCAJan 20 08:50
AA 3207Airbus A319
45m layover

DCAJan 20 09:35
→ORDJan 20 10:52
AA 1200Airbus A319
5h 52m·1 stop
$213 USD
BOSJan 20 08:30
→CLTJan 20 11:09
AA 1004Airbus A321
1h 1m layover

CLTJan 20 12:10
→ORDJan 20 13:22
AA 2236Airbus A321
5h 5m·1 stop
$213 USD
BOSJan 20 16:10
→PHLJan 20 17:53
AA 4561Embraer 175
42m layover

PHLJan 20 18:35
→ORDJan 20 20:15
AA 3177Boeing 737
5h 33m·1 stop
$213 USD
BOSJan 20 16:20
→LGAJan 20 17:46
AA 4620Embraer 175
1h 13m layover

LGAJan 20 18:59
→ORDJan 20 20:53
AA 4353Embraer 175
3h 18m·Nonstop
$278 USD
BOSJan 20 17:42
→ORDJan 20 20:00
AA 4545Embraer 175
3h 14m·Nonstop
$2,363 USD
BOSJan 20 09:51
→ORDJan 20 12:05
AA 4483Embraer 175
3h 12m·Nonstop
$2,363 USD
BOSJan 20 14:43
→ORDJan 20 16:55
AA 3984Embraer 175